Deals on vacations and trips to Windley Key

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Windley Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Link Hotel South Beach

The Link Hotel South Beach

4 out of 5
South Beach
Save 100% on your flight
Price was $949, price is now $544 per person
$544
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
New York (LGA) to Miami (MIA)
This hotel features 2 restaurants and a bar/lounge. Self parking and luggage storage are also offered on site.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $7,134, price is now $2,815 per person
$2,815
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $21,100, price is now $10,604 per person
$10,604
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
This aparthotel features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was $3,113, price is now $1,822 per person
$1,822
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this smoke-free hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and in-room childcare is an added bonus.
EAST Miami Residences

EAST Miami Residences

5 out of 5
Brickell
Save 100% on your flight
Price was $2,399, price is now $1,414 per person
$1,414
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
This luxury hotel features 2 restaurants, 4 outdoor pools, and a 24-hour gym. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and concierge services.

Top Windley Key hotels deals

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
84001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$272 nightly
The price is $306 total per night
$306 total
Aug 10 - Aug 11
Total with taxes and fees
This Art Deco resort features a private beach, a marina, and 4 restaurants. Enjoy a day at the beach snorkeling, or relax with sun loungers. Families will appreciate the arcade/game room and complimentary bicycles.
On private beach
Pool
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$158 nightly
The price is $178 total per night
$178 total
Aug 9 - Aug 10
Total with taxes and fees
A private beach and an outdoor pool are featured at this Art Deco motel. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's no skimping on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking.
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
$149 nightly
The price is $168 total per night
$168 total
Aug 30 - Aug 31
Total with taxes and fees
A marina and an outdoor pool are featured at this hotel. Families will appreciate the children's pool and barbecue grills. Enjoy the gym and free perks like continental breakfast and free self parking.
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$161 nightly
The price is $177 total per night
$177 total
Aug 3 - Aug 4
Total with taxes and fees
An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A business center, a garden, and a picnic area are also on offer.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$208 nightly
The price is $234 total per night
$234 total
Aug 18 - Aug 19
Total with taxes and fees
This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a free kid's club and a playground, and families will appreciate the onsite laundry facilities.
Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Free Cancellation
Reserve now, pay when you stay
$259 nightly
The price is $286 total per night
$286 total
Aug 3 - Aug 4
Total with taxes and fees
This luxury hotel features a private beach, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Family-friendly amenities include an arcade/game room and kid-friendly dining, along with kayaking.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Windley Key attractions

Windley Key Fossil Reef Geological State Park

8.8/10 (184 reviews)
Explore the great outdoors at Windley Key Fossil Reef Geological State Park and enjoy the beautiful sunsets during your trip to Islamorada. Wander the seaside and beautiful beaches in this family-friendly area.
See properties

Frequently asked questions

How much are vacation packages to Windley Key?
Spoil yourself with a memorable travel experience in Windley Key with a vacation package starting at $544. Booking tours, hotels and flights with Travelocity is simple. On top of that, our great deals will leave you with extra cash for plenty of fun times.
Where can I get the best vacation package deals for Windley Key?
Walking away with a great package deal to Windley Key is a breeze with Travelocity. With access to 400 partner airlines and 1,000,000 properties all over the globe, you'll have loads of choice when selecting your flights and hotels.
Why should I purchase my Windley Key vacation package with Travelocity?
Because you'll never roam alone if you book your trip with us, and we offer 24/7 customer support and high-quality service to boot. Add to that our Price Match Guarantee and countless experiences and destinations to select from. We're here to help you have the trip of a lifetime.
Will I save money on my Windley Key car rental if I book it with a hotel or flight?
You certainly can with our Windley Key vacation packages. With one of these, there are tons of ways to stretch your travel budget further. Combine any two or more car, flight, hotel and tour bookings and watch the savings start to pile up. With a rental car, all the landmarks in and around Windley Key are a memorable road trip away.

Photos of local treasures

Browse Windley Key vacation photos for more inspiration

A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.
A forest path surrounded by dense green foliage and trees.
A rocky cliff with intricate erosion patterns and a small cave entrance.
A close-up of a palm plant with long, green leaves against a rocky background.
A forest path surrounded by trees and foliage.

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